Ask A Married Guy: “Should I Tell My Fiancé That I Hooked Up With My Female Friend Before We Met?”

This is our friend Tom. He’s a married guy with tons of relationship experience, and a skilled advice giver who’s here to answer all your pressing sex, dating and relationship questions. Have a query for Tom? Email him at [email protected]! All questions will be posted anonymously, unless otherwise requested.

I’m happily engaged to my boyfriend of four years. About four-and-a-half years ago, my friend Angela and I hooked up, twice. She’s strictly a lesbian, and was single at the time. Too much booze was involved both times, and it was just something that happened that had no strings attached. We remained good friends. Angela and her girlfriend Amy have been together for two years. I see Angela regularly, and Amy occasionally. I genuinely like Amy, and think that she’s a great match for my friend. But I recently learned (through a friend) that Amy is jealous, and doesn’t approve of my friendship with Angela because of our past. This upsets me because Angela and I have no romantic relationship potential or desire. I love my fiancé very much, but we have never discussed past relationships or sexual encounters as Angela and Amy obviously have. I have not yet spoken to Angela about this, and now I feel like I am keeping a secret from my fiancé. Angela is one of two girls I have asked to stand up with me at my wedding next year, and now I’m not so sure where to go from here. Should I talk to her or just try to casually bow out of this friendship? Do I tell my fiancé? – Sarah

Oh, so many secrets. Please leave a copy of your email, in code, on microfilm, up a false chimney, in a barn, in Yemen … IN CASE YOU ARE CAPTURED.

Relax. There’s a lot of smoke billowing from this situation, but not a lot of fire. You can get through this. Let’s break it down:

You love your current partner.

You had an intimate sexual past before you met him.

Congratulations! You are EVERYONE IN A GOOD RELATIONSHIP. But you guys made life harder than it needed to be.I’ll quote you: “We have never discussed past relationships or sexual encounters.” What, like, never? Never ever? You told each other you were sexual innocents, pure as Labrador puppies on a bed of Alpine snow? Unless you’re both sexually aroused by ridiculous “Dawson’s Creek” fantasy scenarios, I call B.S. here.

If I had to guess, from time to time you’ve both casually referenced ex-boy/girlfriends and sexual partners … but then the conversation suddenly felt icky, so you changed the subject. Every single time. For four years. It’s time to exercise some maturity and change that pattern. Amy has done you a favor by letting you lance an uncomfortable boil of secrecy in your life.

First off, you’re not the bad guy. You and your fiancé are equally responsible for this gap in understanding each other’s personal lives. So talk to your fiancé. Set up the conversation with: “I love you. I’m thrilled to be marrying you. But there’s this little thing I have to get off my chest. We don’t talk about our past relationships very much, and in general I think that works great for us. But an issue has come up which makes it me FEEL like I’m keeping secrets, even though based on how we’ve chosen to treat our prior lives, I absolutely was not.” That will terrify him. (Especially if you preface it with “We need to talk.”) He’ll be thinking the worst. Trust me, nothing you say will be as terrifying as the stuff his brain just made up out of thin air. Images of Malaysian sex slavery and German scat clubs will be dancing through his head. So just lay it out the truth. Inside, he’ll be thankful it wasn’t worse.

But don’t do it if you’re not prepared for one of the following:

He’s relieved, because he and his tennis partner Eddie used to blow each other after a few sets, and it MEANT NOTHING.

He’s angry, because he feels foolish at being kept in the dark about a massive part of your relationship with a close friend.

He’s suddenly and furiously interested in all of your sexual partners, and will start yelling a list of names demanding to know if you’ve slept with them. That is his jealous caveman mode, so don’t be surprised to hear things like “you screwed the Postman, didn’t you?”

He shuts down and withdraws. This is the nightmare scenario, because lesbianism can be straight guy Kryptonite. You can understand why. How the hell can we compete with THAT?

In this case, you have to be ready with:

Affirmations that you are not interested in women (it sounds like that’s the case) and 100% committed to him.

Zero (and I mean ZERO) anger … you are foisting this new information on him, so he may lose control of his feelings. You owe him AT LEAST one whole hour of pure compassion, sensitivity and respect. Don’t apologize (again, in the context of your relationship, you didn’t do anything wrong per se), but don’t get defensive, or pull that female emotional judo bullshit where you suddenly make the conversation about HIS failure to be open or HIS secret sexual past. That’s a sneaky chick move and I will be disappointed if you pull it.

Accepting the possibility that he just needs some time to process it. Let him have it. Come back to the issue in a day or two with the same compassion and try to talk through it again. It may take a few tries, but if he’s a decent guy, you can both get over it.

DO NOT tell him anything if you don’t feel emotionally or psychologically capable of dealing with any of the fallout listed above. But if you can, it’s the best thing. Because without the secrecy, your friend’s girlfriend’s jealousy loses all of its power, and becomes the most beautiful thing in the world: someone else’s problem, not yours.